Ethers-buliding-blocks

Annulation-Induced Cascade Transformation of 5-Iodo-1,2,3-triazoles to 2-(1-Aminoalkyl)benzoxazoles was written by Kotovshchikov, Yury N.;Latyshev, Gennadij V.;Navasardyan, Mger A.;Erzunov, Dmitry A.;Beletskaya, Irina P.;Lukashev, Nikolay V.. And the article was included in Organic Letters in 2018.Recommanded Product: 66943-05-3 This article mentions the following:

Base-mediated cyclization of (5-iodo-1,2,3-triazolyl)phenols was proposed as a new synthetic strategy for the in situ generation of diazoimines via electrocyclic ring opening of the fused heterocycle. Cu-catalyzed amination of the intermediate diazoalkanes was employed to develop an efficient cascade approach to functionalized benzoxazoles. In the experiment, the researchers used many compounds, for example, 1,4,7,10-Tetraoxa-13-azacyclopentadecane (cas: 66943-05-3Recommanded Product: 66943-05-3).

1,4,7,10-Tetraoxa-13-azacyclopentadecane (cas: 66943-05-3) belongs to ethers. The oxygen atom in ethers are more electronegative than carbon, thus the hydrogens which are alpha to the ethers are more acidic than the simple hydrocarbons. The unique properties of ethers (i.e., that they are strongly polar, with nonbonding electron pairs but no hydroxyl group) enhance the formation and use of many reagents. For example, Grignard reagents cannot form unless an ether is present to share its lone pair of electrons with the magnesium atom. Complexation of the magnesium atom stabilizes the Grignard reagent and helps to keep it in solution.Recommanded Product: 66943-05-3

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Utilization of the Intramolecular Cycloaddition-Cationic π-Cyclization of an Isomuenchnone Derivative for the Synthesis of (±)-Lycopodine was written by Padwa, Albert;Brodney, Michael A.;Marino, Joseph P. Jr.;Sheehan, Scott M.. And the article was included in Journal of Organic Chemistry in 1997.Application In Synthesis of 3-(3,4-Dimethoxyphenyl)propan-1-ol This article mentions the following:

A new annulation sequence leading to the tetracyclic skeleton of the Lycopodium family of alkaloids is effected by using the tandem cycloaddition-cationic π-cyclization reaction of an isomuenchnone dipole as the key strategic element. Synthesis of the required α-diazo imide precursor involved treating 5-methylcyclohex-2-en-1-one with the organocopper reagent derived from 3-methoxybenzyl chloride in the presence of chlorotrimethylsilane. Ozonolysis of the resulting silyl enol ether followed by a Wittig reaction and conversion to the desired α-diazo imide was carried out using standard malonylacylation and diazotization procedures. Treatment of the α-diazo imide with rhodium(II) perfluorobutyrate afforded a transient 1,3-dipole which subsequently cycloadded across the tethered π-bond. The resulting cycloadduct I was treated with BF₃·2AcOH to give a rearranged tetracyclic compound derived from a Pictet-Spengler-type cyclization of an N-acyliminium ion. The rearranged product was subsequently converted into a key intermediate II previously used for the synthesis of (±)-lycopodine. In the experiment, the researchers used many compounds, for example, 3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3Application In Synthesis of 3-(3,4-Dimethoxyphenyl)propan-1-ol).

3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3) belongs to ethers. Ether is less polar than esters, alcohols or amines because of the oxygen atom that is unable to participate in hydrogen bonding due to the presence of bulky alkyl groups on both sides of the oxygen atom. But ether is more polar than alkenes. The unique properties of ethers (i.e., that they are strongly polar, with nonbonding electron pairs but no hydroxyl group) enhance the formation and use of many reagents. For example, Grignard reagents cannot form unless an ether is present to share its lone pair of electrons with the magnesium atom. Complexation of the magnesium atom stabilizes the Grignard reagent and helps to keep it in solution.Application In Synthesis of 3-(3,4-Dimethoxyphenyl)propan-1-ol

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Bismuth-catalyzed methylation and alkylation of quinone derivatives with tert-butyl peroxybenzoate as an oxidant was written by Yang, Jian;Dong, Yu;He, Shuai;Shi, Zhi-Chuan;Wang, Yu;Wang, Ji-Yu. And the article was included in Tetrahedron in 2019.Formula: C9H10O4 This article mentions the following:

A bismuth-catalyzed methylation of quinones I (R = Me, Bn, H, etc.; R¹ = H, Me; R² = H, Me, Br; R³ = H, Me, Br; R⁴ = H, Me; R⁵ = H), II (R = Me; R⁵ = H; R⁶ = R⁷ = Me, OMe) in the presence of tert-Bu peroxybenzoate (TBPB) was developed via a radical reaction mechanism. Particularly, TBPB was used not only as an efficient oxidant, but also as a green Me source in such transformation. Moreover, this method could also be efficiently extended to the alkylation of quinones I (R = Me, Br, OH; R¹ = R² = R³ = R⁴ = R⁵ = H), II. This reaction tolerated a series of functional groups and prepared a series of vitamin K3 derivatives I (R⁵ = cyclopentyl, cyclohexyl, cyclooctyl, hexan-2-yl, hexan-3-yl) and benzoquinones II (R⁵ = cyclohexyl). Notably, antimalarial parvaquone I (R = OH; R¹ = R² = R³ = R⁴ = H; R⁵ = cyclohexyl) was synthesized by the reaction. In the experiment, the researchers used many compounds, for example, 2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione (cas: 605-94-7Formula: C9H10O4).

2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione (cas: 605-94-7) belongs to ethers. The oxygen atom in ethers are more electronegative than carbon, thus the hydrogens which are alpha to the ethers are more acidic than the simple hydrocarbons. The unique properties of ethers (i.e., that they are strongly polar, with nonbonding electron pairs but no hydroxyl group) enhance the formation and use of many reagents. For example, Grignard reagents cannot form unless an ether is present to share its lone pair of electrons with the magnesium atom. Complexation of the magnesium atom stabilizes the Grignard reagent and helps to keep it in solution.Formula: C9H10O4

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Identification and optimization of novel 1,3,4-oxadiazole EP₁ receptor antagonists was written by Hall, Adrian;Brown, Susan H.;Chowdhury, Anita;Giblin, Gerard M. P.;Gibson, Mairi;Healy, Mark P.;Livermore, David G.;McArthur Wilson, Richard J.;Naylor, Alan;Rawlings, D. Anthony;Roman, Shilina;Ward, Emma;Willay, Caroline. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2007.Formula: C9H10O4 This article mentions the following:

A novel series of oxadiazole EP₁ receptor antagonists was identified by replacing the amide of a known glycine sulfonamide derivative with a 1,3,4-oxadiazole. Optimization of the substitution patterns on the three aromatic rings led to the identification of high affinity EP₁ receptor antagonists. The derivative with highest affinity displayed a binding IC₅₀ of 2.5 nM (pIC₅₀ 8.6). In the experiment, the researchers used many compounds, for example, 2-(4-Methoxyphenoxy)acetic acid (cas: 1877-75-4Formula: C9H10O4).

2-(4-Methoxyphenoxy)acetic acid (cas: 1877-75-4) belongs to ethers. Of all the functional groups, ethers are the least reactive ones. Ether bonds are quite stable towards bases, oxidizing agents and reducing agents. The unique properties of ethers (i.e., that they are strongly polar, with nonbonding electron pairs but no hydroxyl group) enhance the formation and use of many reagents. For example, Grignard reagents cannot form unless an ether is present to share its lone pair of electrons with the magnesium atom. Complexation of the magnesium atom stabilizes the Grignard reagent and helps to keep it in solution.Formula: C9H10O4

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Metal-Cation Recognition in Water by a Tetrapyrazinoporphyrazine-Based Tweezer Receptor was written by Lochman, Lukas;Svec, Jan;Roh, Jaroslav;Kirakci, Kaplan;Lang, Kamil;Zimcik, Petr;Novakova, Veronika. And the article was included in Chemistry – A European Journal in 2016.Electric Literature of C10H21NO4 This article mentions the following:

A series of zinc azaphthalocyanines with two azacrowns in a rigid tweezer arrangement were prepared and the fluorescence sensing properties were studied. The size-driven recognition of alkali and alk. earth metal cations was significantly enhanced by the close cooperation of the two azacrown units, in which both donor nitrogen atoms need to be involved in analyte binding to switch the sensor on. The mono- or biphasic character of the binding isotherms, together with the binding stoichiometry and magnitude of association constants (K_A), indicated specific complexation of particular analytes. Water solvation was shown to play an important role and resulted in a strong quenching of sensor fluorescence in the ON state. The lead compound was embedded into silica nanoparticles and advantageous sensing properties towards K⁺ were demonstrated in water (λ_F = 671 nm, apparent K_A = 82 M^-1, increase of 17×), even in the presence of (supra)physiol. concentrations of Na⁺ and Ca²⁺. In the experiment, the researchers used many compounds, for example, 1,4,7,10-Tetraoxa-13-azacyclopentadecane (cas: 66943-05-3Electric Literature of C10H21NO4).

1,4,7,10-Tetraoxa-13-azacyclopentadecane (cas: 66943-05-3) belongs to ethers. Ether is less polar than esters, alcohols or amines because of the oxygen atom that is unable to participate in hydrogen bonding due to the presence of bulky alkyl groups on both sides of the oxygen atom. At room temperature, ethers are pleasant-smelling colourless liquids. Relative to alcohols, ethers are generally less dense, are less soluble in water, and have lower boiling points. They are relatively unreactive, and as a result they are useful as solvents for fats, oils, waxes, perfumes, resins, dyes, gums, and hydrocarbons. Vapours of certain ethers are used as insecticides, miticides, and fumigants for soil.Electric Literature of C10H21NO4

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Rhodium-Catalyzed Cross-Cyclotrimerization and Dimerization of Allenes with Alkynes was written by Sakashita, Kazuki;Shibata, Yu;Tanaka, Ken. And the article was included in Angewandte Chemie, International Edition in 2016.Synthetic Route of C6H10O2 This article mentions the following:

It has been established that a cationic rhodium(I)/binap complex catalyzed the cross-cyclotrimerization of two mols. of a monosubstituted allene with one mol. of a functionalized alkyne gave 3,6-dialkylidenecyclohex-1-enes. In contrast, the reactions involving di- or trisubstituted allenes and/or unfunctionalized alkynes afforded cross-dimerization products, substituted dendralenes, through β-hydrogen elimination from the corresponding rhodacycles. In the experiment, the researchers used many compounds, for example, 1,4-Dimethoxy-2-butyne (cas: 16356-02-8Synthetic Route of C6H10O2).

1,4-Dimethoxy-2-butyne (cas: 16356-02-8) belongs to ethers. Ether is less polar than esters, alcohols or amines because of the oxygen atom that is unable to participate in hydrogen bonding due to the presence of bulky alkyl groups on both sides of the oxygen atom. The unique properties of ethers (i.e., that they are strongly polar, with nonbonding electron pairs but no hydroxyl group) enhance the formation and use of many reagents. For example, Grignard reagents cannot form unless an ether is present to share its lone pair of electrons with the magnesium atom. Complexation of the magnesium atom stabilizes the Grignard reagent and helps to keep it in solution.Synthetic Route of C6H10O2

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Control of peroxyoxalate chemiluminescence by nitrogen-containing ligand quenching: turning off and on by ligand-metal ion host-guest interactions was written by Maruyama, Takayuki;Fujie, Yasuyuki;Oya, Noriyuki;Hosaka, Eisuke;Kanazawa, Aki;Tanaka, Daisuke;Hattori, Yoshiyuki;Motoyoshiya, Jiro. And the article was included in Tetrahedron in 2011.Quality Control of 1,4,7,10-Tetraoxa-13-azacyclopentadecane This article mentions the following:

The control of peroxyoxalate chemiluminescence (PO-CL) by the coordination of nitrogen-containing ligands and metal cations was investigated. Turning the CL off and on was done by PO-CL using 15-monoazacrown-5-tethered anthracene and alkali metal ions. CL quenching and regeneration was also observed in the separated mol. system of 15-monoazacrown-5 and the fluorophores. CL quenching by a number of ligands bearing dipicolylamino groups was evaluated by these PO-CL reactions and found to be closely related to their oxidation potentials, which is dependent on the Weller rate law for electron exchange and this provides strong support for the existence of the CIEEL PO-CL process. When Zn²⁺ or Cu²⁺ are added to the PO-CL system quenched by the ligand, N-[2-(2,2′-dipicolylamino)ethyl]aniline, CL was turned on because the electron donating ability of the ligands was modulated. This was controlled by the coordination of the studied metal ions and, therefore, this system results in CL because of host-guest interactions. In the experiment, the researchers used many compounds, for example, 1,4,7,10-Tetraoxa-13-azacyclopentadecane (cas: 66943-05-3Quality Control of 1,4,7,10-Tetraoxa-13-azacyclopentadecane).

1,4,7,10-Tetraoxa-13-azacyclopentadecane (cas: 66943-05-3) belongs to ethers. Relative to alcohols, ethers are generally less dense, are less soluble in water, and have lower boiling points. They are relatively unreactive. The unique properties of ethers (i.e., that they are strongly polar, with nonbonding electron pairs but no hydroxyl group) enhance the formation and use of many reagents. For example, Grignard reagents cannot form unless an ether is present to share its lone pair of electrons with the magnesium atom. Complexation of the magnesium atom stabilizes the Grignard reagent and helps to keep it in solution.Quality Control of 1,4,7,10-Tetraoxa-13-azacyclopentadecane

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthesis of tris-(azacrown) ethers for carboxylic acid recognition was written by Lee, Michael;Zali-Boeini, Hassan;Li, Feng;Lindoy, Leonard F.;Jolliffe, Katrina A.. And the article was included in Tetrahedron in 2013.Formula: C10H21NO4 This article mentions the following:

The synergistic enhancement of metal ion extraction by azacrown ethers in the presence of carboxylic acids has been attributed to a ligand assembly effect in which these two ligands form a complex, facilitated by proton transfer, prior to complexation of the metal ion. In order to investigate the first steps in this multi-component complexation procedure, six tris-(azacrown) ethers I [n = 1, 2; R = H, Me, Et] were synthesized in high yields and their ability to complex mono- and tri-carboxylic acids was investigated by ¹H NMR in methanol-d₄. All six compounds bound to benzoic acid with 1:3 host-guest stoichiometry and four of them bound tricarboxylic acids with 1:1 host-guest stoichiometry, providing good support for the proposed first step in the ligand assembly effect. In the experiment, the researchers used many compounds, for example, 1,4,7,10-Tetraoxa-13-azacyclopentadecane (cas: 66943-05-3Formula: C10H21NO4).

1,4,7,10-Tetraoxa-13-azacyclopentadecane (cas: 66943-05-3) belongs to ethers. Of all the functional groups, ethers are the least reactive ones. Ether bonds are quite stable towards bases, oxidizing agents and reducing agents. Electron-deficient reagents are also stabilized by ethers. For example, borane (BH3) is a useful reagent for making alcohols. Pure borane exists as its dimer, diborane (B2H6), a toxic gas that is inconvenient and hazardous to use. Borane forms stable complexes with ethers, however, and it is often supplied and used as its liquid complex with tetrahydrofuran (THF).Formula: C10H21NO4

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Carboxylic Acid-Catalyzed Highly Efficient and Selective Hydroboration of Alkynes with Pinacolborane was written by Ho, Hon Eong;Asao, Naoki;Yamamoto, Yoshinori;Jin, Tienan. And the article was included in Organic Letters in 2014.Electric Literature of C6H10O2 This article mentions the following:

We have demonstrated for the first time that carboxylic acids are able to catalyze the direct hydroboration of various terminal and internal alkynes with pinacolborane, HB(pin), without using any metal catalysts. For example, PhCCB(pin) reacts with HB(pin) in the presence of 4-Me₂NC₆H₄CO₂H giving PhCH:C[B(pin)]₂ in 99% yield. This unprecedented catalytic hydroboration exhibits a broad functional groups compatibility, giving the corresponding alkenyl diboronates and monoboronates in good to high yields with exclusive regio- and stereoselectivities. In the experiment, the researchers used many compounds, for example, 1,4-Dimethoxy-2-butyne (cas: 16356-02-8Electric Literature of C6H10O2).

1,4-Dimethoxy-2-butyne (cas: 16356-02-8) belongs to ethers. The oxygen atom in ethers are more electronegative than carbon, thus the hydrogens which are alpha to the ethers are more acidic than the simple hydrocarbons. Ethers are good solvents partly because they are not very reactive. Most ethers can be cleaved, however, by hydrobromic acid (HBr) to give alkyl bromides or by hydroiodic acid (HI) to give alkyl iodides.Electric Literature of C6H10O2

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem